Structural and mechanistic studies of the copper (II)-assisted ortho-hydroxylation of benzoates by trimethylamine N-oxide

W Buijs, P Comba, D Corneli, H Pritzkow

Index: Buijs, Wim; Comba, Peter; Corneli, Danny; Pritzkow, Hans Journal of Organometallic Chemistry, 2002 , vol. 641, # 1-2 p. 71 - 80

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Citation Number: 20

Abstract

N-benzoyl-2-methylalanine (H2L1) is ortho-hydroxylated stereoselectively by trimethylamine N-oxide (TMAO) in the presence of copper (II). The experimental structure of [Cu (L1)(TMAO) 2] suggests that the oxygen transfer agent TMAO transfers the oxygen atom to copper (II), and (L1) 2−, coordinated to copper (II) by a carboxylate oxygen and the amide nitrogen donor, is well pre-organized for an oxygen transfer from copper to the ortho carbon atom ...

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